#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/53/4025352.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025352
loop_
_publ_author_name
'Leleti Rajender Reddy'
'Sonia G. Das'
'Yugang Liu'
'Mahavir Prashad'
_publ_section_title
;
 A Facile Asymmetric Synthesis of Either Enantiomer of 2-Substituted
 Pyrrolidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2236
_journal_page_last               2246
_journal_paper_doi               10.1021/jo902710s
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H20 Br1 N1 O1 S1'
_chemical_formula_sum            'C14 H20 Br N O S'
_chemical_formula_weight         330.29
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_type_scat_source
'International Tables for Crystallography (Vol C)'
_cell_angle_alpha                90.00
_cell_angle_beta                 112.657(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.3035(5)
_cell_length_b                   5.8935(4)
_cell_length_c                   12.2860(8)
_cell_measurement_reflns_used    5832
_cell_measurement_temperature    150.00(2)
_cell_measurement_theta_max      66
_cell_measurement_theta_min      7
_cell_volume                     755.30(8)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction        'EVALCCD (Duisenberg, 2003)'
_computing_molecular_graphics
;
    ORTEP (Johnson, 1976)
    PLATON (Spek, 1997)
;
_computing_publication_material  'SHELX97(Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELX97 (Sheldrick, 2008)'
_computing_structure_solution
;
 PATTY (DIRDIF99, Beurskins, 1999)
;
_diffrn_ambient_temperature      150.00(2)
_diffrn_measured_fraction_theta_full 0.9802
_diffrn_measured_fraction_theta_max 0.9552
_diffrn_measurement_device_type  Nonius_KappaCCD
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'graphite 002'
_diffrn_radiation_type           CU-K\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5832
_diffrn_reflns_theta_full        46.1
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         6.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.914
_exptl_absorpt_correction_T_max  0.6426
_exptl_absorpt_correction_T_min  0.3059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.32
_refine_ls_abs_structure_details 'Flack H. D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.013(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2343
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.024
_refine_ls_R_factor_gt           0.023
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[σ²(Fo²)+(0.0307P)²+0.0440P] where P=(Fo²+2Fc²)/3  '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.059
_refine_ls_wR_factor_ref         0.059
_reflns_Friedel_coverage         1.0000
_reflns_number_gt                2296
_reflns_number_total             2343
_reflns_threshold_expression     >2.0σ(I)
_cod_data_source_file            jo902710s_si_001.cif
_cod_data_source_block           REDDY2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc ' changed to 'calc'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

data name '_exptl_absorpt__process_details' was replaced with
'_exptl_absorpt_process_details' as specified in the replacement file
'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_formula_sum        'C14 H20 Br1 N1 O1 S1'
_cod_database_code               4025352
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br24 0.52308(2) 0.42735(6) 0.91672(2) 0.03049(10) Uani 1 1 d . . .
S1 0.92943(5) -0.38508(13) 0.71849(5) 0.01941(15) Uani 1 1 d . . .
O1 0.96352(15) -0.5583(4) 0.64723(15) 0.0302(4) Uani 1 1 d . . .
N1 0.84787(18) -0.1705(4) 0.63247(17) 0.0186(5) Uani 1 1 d . . .
C2 0.7060(2) -0.1861(5) 0.6037(2) 0.0196(6) Uani 1 1 d . . .
C3 0.6462(2) -0.1043(6) 0.4754(2) 0.0278(7) Uani 1 1 d . . .
C4 0.7423(2) -0.1813(6) 0.4237(2) 0.0324(7) Uani 1 1 d . . .
C5 0.8701(2) -0.1235(5) 0.5226(2) 0.0266(8) Uani 1 1 d . . .
C11 1.0807(2) -0.2445(5) 0.8111(2) 0.0231(6) Uani 1 1 d . . .
C12 1.1439(2) -0.1221(6) 0.7382(3) 0.0368(9) Uani 1 1 d . . .
C13 1.1637(2) -0.4381(6) 0.8823(2) 0.0335(7) Uani 1 1 d . . .
C14 1.0481(2) -0.0786(7) 0.8905(2) 0.0357(7) Uani 1 1 d . . .
C21 0.66702(19) -0.0424(5) 0.68604(18) 0.0185(6) Uani 1 1 d . . .
C22 0.7226(2) 0.1674(5) 0.7240(2) 0.0190(6) Uani 1 1 d . . .
C23 0.6816(2) 0.3073(5) 0.7937(2) 0.0217(6) Uani 1 1 d . . .
C24 0.5822(2) 0.2322(5) 0.8240(2) 0.0195(6) Uani 1 1 d . . .
C25 0.5257(2) 0.0235(5) 0.7895(2) 0.0233(7) Uani 1 1 d . . .
C26 0.5685(2) -0.1119(5) 0.7207(2) 0.0207(7) Uani 1 1 d . . .
H2 0.6816 -0.3478 0.6085 0.023 Uiso 1 1 calc R . .
H22 0.7902 0.2169 0.7019 0.023 Uiso 1 1 calc R . .
H23 0.7207 0.4506 0.8198 0.026 Uiso 1 1 calc R . .
H25 0.4588 -0.0261 0.8125 0.028 Uiso 1 1 calc R . .
H26 0.5300 -0.2562 0.6961 0.025 Uiso 1 1 calc R . .
H3A 0.5613 -0.1751 0.4333 0.033 Uiso 1 1 calc R . .
H3B 0.6365 0.0628 0.4714 0.033 Uiso 1 1 calc R . .
H4A 0.7308 -0.0972 0.3506 0.039 Uiso 1 1 calc R . .
H4B 0.7349 -0.3460 0.4068 0.039 Uiso 1 1 calc R . .
H5A 0.9398 -0.2199 0.5182 0.032 Uiso 1 1 calc R . .
H5B 0.8925 0.0379 0.5187 0.032 Uiso 1 1 calc R . .
H12A 1.2296 -0.0708 0.7901 0.055 Uiso 1 1 calc R . .
H12B 1.0917 0.0092 0.6989 0.055 Uiso 1 1 calc R . .
H12C 1.1511 -0.2261 0.6788 0.055 Uiso 1 1 calc R . .
H13A 1.1815 -0.5441 0.8291 0.050 Uiso 1 1 calc R . .
H13B 1.1185 -0.5179 0.9248 0.050 Uiso 1 1 calc R . .
H13C 1.2446 -0.3771 0.9390 0.050 Uiso 1 1 calc R . .
H14A 0.9999 -0.1577 0.9305 0.054 Uiso 1 1 calc R . .
H14B 0.9960 0.0455 0.8428 0.054 Uiso 1 1 calc R . .
H14C 1.1274 -0.0169 0.9495 0.054 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_radius_bond
Br 1.14
S 1.02
O 0.73
N 0.75
C 0.77
H 0.32
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 110.51(11) . . . ?
O1 S1 C11 106.39(11) . . . ?
N1 S1 C11 101.76(12) . . . ?
C5 N1 C2 109.52(18) . . . ?
C5 N1 S1 117.85(16) . . . ?
C2 N1 S1 112.26(17) . . . ?
N1 C2 C21 111.6(2) . . . ?
N1 C2 C3 103.29(19) . . . ?
C21 C2 C3 112.7(2) . . . ?
N1 C2 H2 109.70 . . . ?
C21 C2 H2 109.70 . . . ?
C3 C2 H2 109.70 . . . ?
C4 C3 C2 103.4(2) . . . ?
C4 C3 H3A 111.10 . . . ?
C2 C3 H3A 111.10 . . . ?
C4 C3 H3B 111.10 . . . ?
C2 C3 H3B 111.10 . . . ?
H3A C3 H3B 109.00 . . . ?
C3 C4 C5 102.1(2) . . . ?
C3 C4 H4A 111.30 . . . ?
C5 C4 H4A 111.30 . . . ?
C3 C4 H4B 111.30 . . . ?
C5 C4 H4B 111.30 . . . ?
H4A C4 H4B 109.20 . . . ?
N1 C5 C4 103.98(19) . . . ?
N1 C5 H5A 111.00 . . . ?
C4 C5 H5A 111.00 . . . ?
N1 C5 H5B 111.00 . . . ?
C4 C5 H5B 111.00 . . . ?
H5A C5 H5B 109.00 . . . ?
C13 C11 C14 111.1(2) . . . ?
C13 C11 C12 111.6(2) . . . ?
C14 C11 C12 110.9(3) . . . ?
C13 C11 S1 103.8(2) . . . ?
C14 C11 S1 106.73(16) . . . ?
C12 C11 S1 112.51(19) . . . ?
C11 C12 H12A 109.50 . . . ?
C11 C12 H12B 109.50 . . . ?
H12A C12 H12B 109.50 . . . ?
C11 C12 H12C 109.50 . . . ?
H12A C12 H12C 109.50 . . . ?
H12B C12 H12C 109.50 . . . ?
C11 C13 H13A 109.50 . . . ?
C11 C13 H13B 109.50 . . . ?
H13A C13 H13B 109.50 . . . ?
C11 C13 H13C 109.50 . . . ?
H13A C13 H13C 109.50 . . . ?
H13B C13 H13C 109.50 . . . ?
C11 C14 H14A 109.50 . . . ?
C11 C14 H14B 109.50 . . . ?
H14A C14 H14B 109.50 . . . ?
C11 C14 H14C 109.50 . . . ?
H14A C14 H14C 109.50 . . . ?
H14B C14 H14C 109.50 . . . ?
C22 C21 C26 118.1(2) . . . ?
C22 C21 C2 121.0(2) . . . ?
C26 C21 C2 120.8(3) . . . ?
C21 C22 C23 121.4(2) . . . ?
C21 C22 H22 119.30 . . . ?
C23 C22 H22 119.30 . . . ?
C24 C23 C22 118.2(3) . . . ?
C24 C23 H23 120.90 . . . ?
C22 C23 H23 120.90 . . . ?
C25 C24 C23 122.1(2) . . . ?
C25 C24 Br24 119.64(18) . . . ?
C23 C24 Br24 118.3(2) . . . ?
C24 C25 C26 118.4(2) . . . ?
C24 C25 H25 120.80 . . . ?
C26 C25 H25 120.80 . . . ?
C25 C26 C21 121.7(3) . . . ?
C25 C26 H26 119.10 . . . ?
C21 C26 H26 119.10 . . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br24 C24 1.911(3) . . ?
S1 O1 1.489(2) . . ?
S1 N1 1.678(2) . . ?
S1 C11 1.845(2) . . ?
N1 C5 1.491(3) . . ?
N1 C2 1.506(3) . . ?
C2 C21 1.510(3) . . ?
C2 C3 1.534(3) . . ?
C2 H2 1.0000 . . ?
C3 C4 1.523(4) . . ?
C3 H3A 0.9900 . . ?
C3 H3B 0.9900 . . ?
C4 C5 1.525(3) . . ?
C4 H4A 0.9900 . . ?
C4 H4B 0.9900 . . ?
C5 H5A 0.9900 . . ?
C5 H5B 0.9900 . . ?
C11 C13 1.522(4) . . ?
C11 C14 1.524(4) . . ?
C11 C12 1.525(4) . . ?
C12 H12A 0.9800 . . ?
C12 H12B 0.9800 . . ?
C12 H12C 0.9800 . . ?
C13 H13A 0.9800 . . ?
C13 H13B 0.9800 . . ?
C13 H13C 0.9800 . . ?
C14 H14A 0.9800 . . ?
C14 H14B 0.9800 . . ?
C14 H14C 0.9800 . . ?
C21 C22 1.384(4) . . ?
C21 C26 1.398(3) . . ?
C22 C23 1.391(4) . . ?
C22 H22 0.9500 . . ?
C23 C24 1.386(3) . . ?
C23 H23 0.9500 . . ?
C24 C25 1.375(4) . . ?
C25 C26 1.379(4) . . ?
C25 H25 0.9500 . . ?
C26 H26 0.9500 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C5 -26.6(2) . . . . ?
C11 S1 N1 C5 86.07(19) . . . . ?
O1 S1 N1 C2 102.04(17) . . . . ?
C11 S1 N1 C2 -145.29(18) . . . . ?
C5 N1 C2 C21 -130.9(2) . . . . ?
S1 N1 C2 C21 96.2(2) . . . . ?
C5 N1 C2 C3 -9.6(3) . . . . ?
S1 N1 C2 C3 -142.5(2) . . . . ?
N1 C2 C3 C4 32.0(3) . . . . ?
C21 C2 C3 C4 152.5(2) . . . . ?
C2 C3 C4 C5 -42.2(3) . . . . ?
C2 N1 C5 C4 -16.4(3) . . . . ?
S1 N1 C5 C4 113.5(2) . . . . ?
C3 C4 C5 N1 35.9(3) . . . . ?
O1 S1 C11 C13 -58.64(19) . . . . ?
N1 S1 C11 C13 -174.38(17) . . . . ?
O1 S1 C11 C14 -176.1(2) . . . . ?
N1 S1 C11 C14 68.2(2) . . . . ?
O1 S1 C11 C12 62.1(2) . . . . ?
N1 S1 C11 C12 -53.6(2) . . . . ?
N1 C2 C21 C22 38.1(3) . . . . ?
C3 C2 C21 C22 -77.6(3) . . . . ?
N1 C2 C21 C26 -145.6(2) . . . . ?
C3 C2 C21 C26 98.7(3) . . . . ?
C26 C21 C22 C23 -0.6(4) . . . . ?
C2 C21 C22 C23 175.8(2) . . . . ?
C21 C22 C23 C24 -0.5(4) . . . . ?
C22 C23 C24 C25 1.4(4) . . . . ?
C22 C23 C24 Br24 -178.55(18) . . . . ?
C23 C24 C25 C26 -1.3(4) . . . . ?
Br24 C24 C25 C26 178.71(18) . . . . ?
C24 C25 C26 C21 0.2(4) . . . . ?
C22 C21 C26 C25 0.7(4) . . . . ?
C2 C21 C26 C25 -175.7(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 46188679
